
Retire With Purpose - The Retirement Podcast
Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and Founder of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you’ve always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2024 HOWARD BAILEY FINANCIAL, INC.
Latest episodes

Jun 6, 2025 • 17min
503: Investing at the Sleeping Point: Finding Peace in Your Portfolio
After a sharp rebound in the market, you may still feel the lingering effects of recent volatility. But before the next tide of turmoil, now is an ideal time to deploy the "Sleeping Point" Strategy: adjusting your portfolio to a level where you can sleep soundly at night. In this episode, we discuss: The importance of reducing risk before panic How to embrace proactive planning The danger of over-investing How (and when) to stress test your portfolio Today's article is from Pearl's Prime Cuts blog titled, A Good Time for the Sleeping Point Story. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: RetireWithPurpose.com/503 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu 📅 SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3z5mXIw ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

17 snips
May 30, 2025 • 28min
502: Freedom After 50: The Hidden Cost of Delayed Gratification in Retirement
Les McDaniel, a certified retirement coach at Howard Bailey Financial, joins the discussion on how a lifetime of delayed gratification can become a hurdle in retirement. He explores the psychology behind postponement and the importance of shifting from saving to enjoying life. The concept of a 'joy budget' is introduced, offering tools to reframe spending and enhance personal fulfillment. Listeners learn about the balance between enjoyment and savings while uncovering strategies for personal growth and connection through tradition and heirlooms.

17 snips
May 23, 2025 • 24min
501: The Four Futures of Retirement: Which Path Are You On?
Explore the unpredictable nature of retirement and the importance of planning for various potential futures. Learn how to adapt to life's curveballs while managing common concerns like financial insecurity. Discover insights from futurists and strategies to create a comprehensive retirement plan that accounts for both expected and unexpected challenges. Embrace a proactive mindset as you consider the macro forces shaping your future and the advantages of collaborating with a financial advisor.

May 16, 2025 • 39min
500: Freedom After 50: 6 Crucial Signs You're Ready for a New Direction
Les McDaniel, a certified retirement coach at Howard Bailey Financial, guides listeners through the transformative journey after 50. He emphasizes the importance of tuning into one's intuition and recognizing the signs that signal it's time for a new direction. The discussion covers daily practices for reconnecting with purpose, the detrimental effects of negativity, and ways to embrace simple joys. McDaniel shares techniques for overcoming emotional unrest in retirement and highlights the power of small, intentional actions to foster fulfillment and happiness.

9 snips
May 12, 2025 • 57min
499: Retirement Income Strategies to Quell Inflation Fears and Spend Comfortably with David Blanchett
David Blanchett, Managing Director at PGIM DC Solutions and a leading voice in retirement income planning, returns with fresh insights. He tackles the misunderstood 'retirement crisis,' advocating for a view of it as a 'challenge' instead. The conversation dives into adapting the 4% withdrawal rule amidst changing economic conditions, emphasizing personalized retirement strategies. Blanchett also highlights the transformative role of guaranteed income annuities and the essential need for realistic spending patterns in an inflationary environment.

13 snips
May 9, 2025 • 25min
498: 4 Ways to Cultivate Character Amid Market Chaos
The discussion centers on turning market chaos into personal growth opportunities. Stress can be reinterpreted as a catalyst for thoughtful decision-making. A jazz analogy illustrates the importance of adaptability in financial choices. A four-step framework promotes character development during uncertainty. The speakers advocate for reflection to enhance investment strategies. Mindful decision-making techniques are shared, emphasizing emotional regulation during stressful times and prioritizing life's overall value over just financial gains.

12 snips
May 2, 2025 • 39min
497: Freedom After 50: 5 Numbers Stealing Your Time, Wealth, and Joy
Les McDaniel, a certified retirement coach from Howard Bailey Financial, shares valuable insights on aligning financial strategies with personal values. He discusses the transformative 50/30/20 budgeting rule and how it relates to life satisfaction. McDaniel emphasizes the importance of meaningful versus meaningless time in retirement and introduces the Satisfaction Ratio to enhance joy in daily life. Listeners are encouraged to reassess expectations and prioritize empowerment through financial choices, fostering a life rich in purpose.

16 snips
Apr 25, 2025 • 23min
496: Claiming Social Security Early: Is it the Right Strategy for You?
The debate on the ideal age to claim Social Security unfolds, challenging the conventional wisdom of waiting until 70. Discover the benefits of filing early and how individual circumstances can shift the optimal claiming age. Understand the concept of a 'breakeven' point when comparing early versus delayed benefits. Delve into personalized strategies that cater to specific financial situations, particularly for singles or widowed individuals. Ultimately, learn how claiming benefits early can enhance your retirement income.

23 snips
Apr 18, 2025 • 35min
495: Freedom After 50: The World is Ending… What’s Next?
Les McDaniel, a certified retirement coach and the chief purpose officer at Howard Bailey Financial, joins Casey Weade to tackle profound existential questions about life and contentment. They dive into the impact of letting go of control and embracing uncertainty. Discover how the pursuit of pure contentment outweighs chasing fleeting happiness. The duo shares five thought-provoking questions designed to help listeners cultivate mindfulness and joy in the present, all while navigating life's complexities.

19 snips
Apr 14, 2025 • 1h 9min
494: Beyond the Headlines: How Retirees Can Navigate Investment Risks with Larry Swedroe
In this discussion with Larry Swedroe, former Chief Research Officer at Buckingham Strategic Wealth and author of over 18 books, listeners dive deep into the world of evidence-based investing. Larry emphasizes the power of passive investing and its role in wealth-building. He discusses common emotional biases that lead to poor investment decisions and highlights the importance of a globally diversified portfolio. With insights on risk versus uncertainty, he provides retirees with essential strategies to navigate investment challenges confidently.